The last time I went to Chicago I saw Desperately Seeking Susan in the theater, and it was a new release at the time. Also, I was at an age where getting to see Desperately Seeking Susan was the coolest, and I spent my allowance on a bunch of Madonna-inspired rubber and silver bracelets at Contempo Casuals at Water Tower Place, oblivious to the amazing city around me. Luckily this past weekend, I returned to Chicago more mature and appreciative of architecture, and I found myself cruising Trulia for Chicago housing as soon as I had to leave. Here are just a few of the sites that make up the amazing city.

One of the most fun things you can do in Chicago is rent a bike and take it up or down the coast of Lake Michigan; we opted to go North. It was worth the horrendous customer service and outrageous prices at the bike rental place on the Navy Pier.

One of the great things about the architecture of Chicago is all of those little details on the buildings that came before Mies stripped everything down. The detail above is from what is currently a Bloomingdale’s Home store, formerly the Medinah Temple, designed by Huehl and Schmid, built in 1912.

While I knew a bit about the 1922 Chicago Tribune building/contest (in architecture school you learn that the second-place entry is the one everyone is still talking about, by Eliel Saarninen). What I didn’t realize is that the existing neo-gothic architecture has all of these little fragments from other buildings around the world stuck in it, from castles in England to the Great Wall of China.

Okay, so I was not coordinated enough to ride my bike and snap a picture of 860-880 Lake Shore Drive at the same time, so they are missing from this photo essay, as well as a slew of other iconic buildings. Sorry! Anyway, Marnia City (1959) by a.k.a. the honeycomb buildings, was built by one of Mies’ proteges, Bertrand Goldberg.

He also designed the Prentice Women’s Hospital, a Brutalist building that is currently in danger of being demolished (last I heard Northwestern University was still pushing to tear it down; sign a petition to help it get landmark status here). This building is a feat of engineering and was one of the first designs to use CAD, which was cutting edge technology at the time. The building was completed in 1975.

I think I like this view of Frank Gehry’s Jay Pritzker Pavilion at Millennium Park (2004) the best. He sure knows how to make you want to go check out what the rest of it looks like with a big metal tease. Here’s what the rest of it looks like.